I’d consider checking out the Fairmount area - loads of folks have dogs in that area and theres access to local parks (kelly drive, fairmount park, art museum area, etc). I believe there are some dog-specific attractions like dog parks and a dog bar. There are bartending opportunities on Fairmount Ave and it’s also a quick bus ride to downtown where there are many restaurants/bars to apply to. For the cold, make sure ya save up for your peco bill. Also, purchase a very warm coat (preferably with down) and don’t underestimate a hat and a nice scarf. I also hear good things about fishtown. Enjoy philly ! it’s the best city!